5-Amino-4,6-dichloropyrimidine → 2-(2,6-Dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide

HRID 2063512

반응식

HRID 2063512 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](Cl)=[O:11].[Cl:13][C:14]1[C:19]([NH2:20])=[C:18]([Cl:21])[N:17]=[CH:16][N:15]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:20][C:19]1[C:14]([Cl:13])=[N:15][CH:16]=[N:17][C:18]=1[Cl:21])=[O:11]

참가 물질

3

반응물 2

HCID 794345-Amino-4,6-dichloropyrimidineHCID 27581482-(2,6-Dichlorophenyl)acetyl chloride

생성물 1

HCID 577424622-(2,6-Dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide수율 84%

반응 조건

온도
130 °C

실험 절차

To a mixture of 2,6-dichlorophenyl acetic acid (100 g, 487 mmol) and DMF (1.5 mL) in toluene (600 mL) was added thionyl chloride (116 g, 974 mmol). The resulting mixture was stirred at rt. After 12 h, the solution was concentrated to provide 2,6-dichloro-phenylacetyl chloride as colorless oil. MS (ESI): mass calcd. for C8H5Cl3O, 221.94; m/z found, 223.0 [M+H]+. 1H NMR (CDCl3): 7.33 (d, J=8.1 Hz, 2H), 7.29-7.24 (m, 1H), 4.56 (s, 2H). A suspension of the crude 2,6-dichloro-phenylacetyl chloride and 4,6-dichloro-pyrimidin-5-ylamine (76 g, 463 mmol) was heated neat to 130° C. After 1 h, the resulting solid was cooled, collected by filtration, and washed with cold MeOH (400 mL) to provide the title compound as a solid (135 g, 84%). MS (ESI): mass calcd. for C12H7Cl4N3O, 348.9; m/z found, 350.0 [M+H]+. 1H NMR ((CD3)2SO): 10.59 (s, 1H), 8.86 (s, 1H), 7.50 (d, J=8.0 Hz, 2H), 7.37-7.33 (m, 1H), 4.13 (s, 2H).

후처리

  1. temperaturethe resulting solid was cooled
  2. filtrationcollected by filtration
  3. washwashed with cold MeOH (400 mL)

출처 및 근거

ORD 기록
ord-bd7bd1bb4f7d47019a3a53205e48fabc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288397B2

연결된 노트

불러오는 중…